WO2016094161A1 - Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen - Google Patents
Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen Download PDFInfo
- Publication number
- WO2016094161A1 WO2016094161A1 PCT/US2015/063612 US2015063612W WO2016094161A1 WO 2016094161 A1 WO2016094161 A1 WO 2016094161A1 US 2015063612 W US2015063612 W US 2015063612W WO 2016094161 A1 WO2016094161 A1 WO 2016094161A1
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- WIPO (PCT)
- Prior art keywords
- oil
- butylperoxy
- elastomer
- rubber
- elastomer composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 200
- 238000000034 method Methods 0.000 title claims abstract description 61
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 39
- 239000001301 oxygen Substances 0.000 title claims abstract description 39
- 229920000642 polymer Polymers 0.000 title claims description 29
- 238000004132 cross linking Methods 0.000 title claims description 28
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- 239000000806 elastomer Substances 0.000 claims abstract description 141
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 79
- 238000009472 formulation Methods 0.000 claims abstract description 77
- 238000001035 drying Methods 0.000 claims abstract description 50
- 150000003254 radicals Chemical class 0.000 claims abstract description 41
- 230000008569 process Effects 0.000 claims abstract description 18
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- -1 diperoxyketals Chemical class 0.000 claims description 80
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- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 239000011593 sulfur Substances 0.000 claims description 30
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 27
- 229920002943 EPDM rubber Polymers 0.000 claims description 25
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 25
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000945 filler Substances 0.000 claims description 19
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- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 12
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 11
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 claims description 11
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 11
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 10
- FCHGUOSEXNGSMK-UHFFFAOYSA-N 1-tert-butylperoxy-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1C(C)C FCHGUOSEXNGSMK-UHFFFAOYSA-N 0.000 claims description 10
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- 229940099514 low-density polyethylene Drugs 0.000 claims description 8
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- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 claims description 8
- 229920002379 silicone rubber Polymers 0.000 claims description 8
- 244000043261 Hevea brasiliensis Species 0.000 claims description 7
- 229920005560 fluorosilicone rubber Polymers 0.000 claims description 7
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- 150000008117 polysulfides Polymers 0.000 claims description 7
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
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- 229920002449 FKM Polymers 0.000 claims description 6
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- 235000019498 Walnut oil Nutrition 0.000 claims description 6
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- 229920001084 poly(chloroprene) Polymers 0.000 claims description 6
- 235000005713 safflower oil Nutrition 0.000 claims description 6
- 239000003813 safflower oil Substances 0.000 claims description 6
- 239000004945 silicone rubber Substances 0.000 claims description 6
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 6
- 239000008170 walnut oil Substances 0.000 claims description 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 5
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 239000012933 diacyl peroxide Substances 0.000 claims description 5
- 125000005634 peroxydicarbonate group Chemical group 0.000 claims description 5
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- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
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- CTQBRSUCLFHKGM-UHFFFAOYSA-N tetraoxolan-5-one Chemical class O=C1OOOO1 CTQBRSUCLFHKGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 claims description 3
- 229920006169 Perfluoroelastomer Polymers 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical class C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004814 polyurethane Substances 0.000 claims description 2
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 claims description 2
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 claims description 2
- 241001125048 Sardina Species 0.000 claims 3
- 229920006168 hydrated nitrile rubber Polymers 0.000 claims 2
- 229920003192 poly(bis maleimide) Polymers 0.000 claims 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 125000000746 allylic group Chemical group 0.000 claims 1
- WXCZUWHSJWOTRV-UHFFFAOYSA-N but-1-ene;ethene Chemical compound C=C.CCC=C WXCZUWHSJWOTRV-UHFFFAOYSA-N 0.000 claims 1
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
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- 238000012360 testing method Methods 0.000 description 26
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- 230000001815 facial effect Effects 0.000 description 13
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- HARQWLDROVMFJE-UHFFFAOYSA-N ethyl 3,3-bis(tert-butylperoxy)butanoate Chemical compound CCOC(=O)CC(C)(OOC(C)(C)C)OOC(C)(C)C HARQWLDROVMFJE-UHFFFAOYSA-N 0.000 description 5
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- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
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- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- GLOYGJPNNKTDIG-UHFFFAOYSA-N SC=1N=NSC=1S Chemical class SC=1N=NSC=1S GLOYGJPNNKTDIG-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
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- PNBJAGVFDMLGSZ-UHFFFAOYSA-N [3-tert-butyl-2-(3-tert-butyl-4-methyl-2-phenylpent-4-en-2-yl)peroxy-4-methylpent-4-en-2-yl]benzene Chemical compound C(C)(C)(C)C(C(C)(C1=CC=CC=C1)OOC(C(C(C)(C)C)C(=C)C)(C)C1=CC=CC=C1)C(=C)C PNBJAGVFDMLGSZ-UHFFFAOYSA-N 0.000 description 1
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- KGQLBLGDIQNGSB-UHFFFAOYSA-N benzene-1,4-diol;methoxymethane Chemical compound COC.OC1=CC=C(O)C=C1 KGQLBLGDIQNGSB-UHFFFAOYSA-N 0.000 description 1
- IKMNXRVKWDYWDZ-UHFFFAOYSA-N benzylcarbamothioyl n-benzylcarbamodithioate Chemical compound C=1C=CC=CC=1CNC(=S)SC(=S)NCC1=CC=CC=C1 IKMNXRVKWDYWDZ-UHFFFAOYSA-N 0.000 description 1
- VKLBNKCWILJHLW-UHFFFAOYSA-N benzylcarbamothioylsulfanyl n-benzylcarbamodithioate Chemical compound C=1C=CC=CC=1CNC(=S)SSC(=S)NCC1=CC=CC=C1 VKLBNKCWILJHLW-UHFFFAOYSA-N 0.000 description 1
- NFZRSOHGHXZUPA-UHFFFAOYSA-N bis(2-methylpropyl)carbamothioyl n,n-bis(2-methylpropyl)carbamodithioate Chemical compound CC(C)CN(CC(C)C)C(=S)SC(=S)N(CC(C)C)CC(C)C NFZRSOHGHXZUPA-UHFFFAOYSA-N 0.000 description 1
- QOTYLQBPNZRMNL-UHFFFAOYSA-N bis(2-methylpropyl)carbamothioylsulfanyl n,n-bis(2-methylpropyl)carbamodithioate Chemical compound CC(C)CN(CC(C)C)C(=S)SSC(=S)N(CC(C)C)CC(C)C QOTYLQBPNZRMNL-UHFFFAOYSA-N 0.000 description 1
- USBHFGNOYVOTON-UHFFFAOYSA-K bis(dimethylcarbamothioylsulfanyl)bismuthanyl n,n-dimethylcarbamodithioate Chemical compound [Bi+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S USBHFGNOYVOTON-UHFFFAOYSA-K 0.000 description 1
- KDQZPXCKTHKGQM-UHFFFAOYSA-L bis(dipentylcarbamothioylsulfanyl)lead Chemical compound [Pb+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC KDQZPXCKTHKGQM-UHFFFAOYSA-L 0.000 description 1
- PAKRLBFYNABWNT-UHFFFAOYSA-N butyl 4,4-bis(2-methylbutan-2-ylperoxy)pentanoate Chemical compound CCCCOC(=O)CCC(C)(OOC(C)(C)CC)OOC(C)(C)CC PAKRLBFYNABWNT-UHFFFAOYSA-N 0.000 description 1
- GAQHRUGINNUYSO-UHFFFAOYSA-L cadmium(2+);n,n-dipentylcarbamodithioate Chemical compound [Cd+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC GAQHRUGINNUYSO-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- NRIQJFWHPUCFPA-UHFFFAOYSA-N carbamothioyl n-(2-methylpropyl)carbamodithioate Chemical compound CC(C)CNC(=S)SC(N)=S NRIQJFWHPUCFPA-UHFFFAOYSA-N 0.000 description 1
- JGADIHBOLVFLCA-UHFFFAOYSA-N carbamothioylsulfanyl n-(2-methylpropyl)carbamodithioate Chemical compound CC(C)CNC(=S)SSC(N)=S JGADIHBOLVFLCA-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000012669 compression test Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- KSXWJZKMQSIXTJ-UHFFFAOYSA-L copper;2-sulfanyl-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Cu+2].C1=CC=C2SC(C(=O)[O-])(S)NC2=C1.C1=CC=C2SC(C(=O)[O-])(S)NC2=C1 KSXWJZKMQSIXTJ-UHFFFAOYSA-L 0.000 description 1
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- WITDFSFZHZYQHB-UHFFFAOYSA-N dibenzylcarbamothioylsulfanyl n,n-dibenzylcarbamodithioate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=S)SSC(=S)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WITDFSFZHZYQHB-UHFFFAOYSA-N 0.000 description 1
- LEOJDCQCOZOLTQ-UHFFFAOYSA-N dibutylcarbamothioyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SC(=S)N(CCCC)CCCC LEOJDCQCOZOLTQ-UHFFFAOYSA-N 0.000 description 1
- RLULIUSIDLLCSW-UHFFFAOYSA-N diethylcarbamothioylsulfanylselanyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)S[Se]SC(=S)N(CC)CC RLULIUSIDLLCSW-UHFFFAOYSA-N 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
- QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
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- 229950004394 ditiocarb Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
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- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- NICWAKGKDIAMOD-UHFFFAOYSA-N ethyl 3,3-bis(2-methylbutan-2-ylperoxy)butanoate Chemical compound CCOC(=O)CC(C)(OOC(C)(C)CC)OOC(C)(C)CC NICWAKGKDIAMOD-UHFFFAOYSA-N 0.000 description 1
- 229920006229 ethylene acrylic elastomer Polymers 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 1
- 239000005043 ethylene-methyl acrylate Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QGTHALAWFUFVCU-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;lead(2+) Chemical compound [Pb+2].CN(C)C([S-])=S.CN(C)C([S-])=S QGTHALAWFUFVCU-UHFFFAOYSA-L 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940032017 n-oxydiethylene-2-benzothiazole sulfenamide Drugs 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- QCAZHHXMIVSLMW-UHFFFAOYSA-N o-butyl (butoxycarbothioyldisulfanyl)methanethioate Chemical compound CCCCOC(=S)SSC(=S)OCCCC QCAZHHXMIVSLMW-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- ZSBDGXGICLIJGD-UHFFFAOYSA-N p-phenoxyphenol Natural products C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PVFZKRMYBKEXBN-UHFFFAOYSA-N piperidine;piperidine-1-carbodithioic acid Chemical compound C1CCNCC1.SC(=S)N1CCCCC1 PVFZKRMYBKEXBN-UHFFFAOYSA-N 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- VLDHWMAJBNWALQ-UHFFFAOYSA-N sodium;3h-1,3-benzothiazole-2-thione Chemical compound [Na+].C1=CC=C2SC(S)=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-N 0.000 description 1
- HUMLQUKVJARKRN-UHFFFAOYSA-M sodium;n,n-dibutylcarbamodithioate Chemical compound [Na+].CCCCN(C([S-])=S)CCCC HUMLQUKVJARKRN-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- SUEGWIXYCHISPX-UHFFFAOYSA-N sulfane trihydroxy(sulfanylidene)-lambda5-phosphane Chemical compound OP(O)(O)=S.S SUEGWIXYCHISPX-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- GOQCSVOOQKFAKT-UHFFFAOYSA-L zinc;n,n-bis(2-methylpropyl)carbamodithioate Chemical compound [Zn+2].CC(C)CN(C([S-])=S)CC(C)C.CC(C)CN(C([S-])=S)CC(C)C GOQCSVOOQKFAKT-UHFFFAOYSA-L 0.000 description 1
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
- JGSUMMPGKPITGK-UHFFFAOYSA-L zinc;n,n-dipentylcarbamodithioate Chemical compound [Zn+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC JGSUMMPGKPITGK-UHFFFAOYSA-L 0.000 description 1
- SZNCKQHFYDCMLZ-UHFFFAOYSA-L zinc;propan-2-yloxymethanedithioate Chemical compound [Zn+2].CC(C)OC([S-])=S.CC(C)OC([S-])=S SZNCKQHFYDCMLZ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
- B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
- B29C35/04—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould using liquids, gas or steam
- B29C35/045—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould using liquids, gas or steam using gas or flames
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
- B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
- B29C35/04—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould using liquids, gas or steam
- B29C35/049—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould using liquids, gas or steam using steam or damp
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
- B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
- B29C35/08—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
- B29C35/0805—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/022—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the choice of material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
- B29C71/04—After-treatment of articles without altering their shape; Apparatus therefor by wave energy or particle radiation, e.g. for curing or vulcanising preformed articles
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- C—CHEMISTRY; METALLURGY
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Definitions
- the present invention relates to compositions and methods for crosslinking polymers in the presence of atmospheric oxygen and to products made by those methods.
- Embodiments of the present invention relate to an organic peroxide formulation comprising, consisting essentially of, or consisting of:
- Illustrative monoperoxy carbonates include:
- organic peroxide formulations of the present invention may further include at least one inert filler, such as silica filler.
- drying oils may include oils derived from plant, animal, and fish sources including, for example, glycerol triesters of fatty acids which are characterized by relatively high levels of polyunsaturated fatty acids, especially eleostearic acid and alpha- linolenic acid.
- Non-limiting examples of suitable inert fillers for use in the organic peroxide formulations of the present invention include water washed clay, e.g., Burgess Clay, precipitated silica, precipitated calcium carbonate, synthetic calcium silicate, and combinations thereof.
- Various combinations of these fillers can be used by one skilled in the art to achieve a free-flowing, non-caking final peroxide formulation.
- the amount of filler in the organic peroxide formulation can range from about 0.1 wt to about 90 wt , depending upon the type of peroxide and additives used, more preferably from about 0.5 wt to about 70 wt , most preferably from about 1 wt to about 60%.
- the extruded profile is heated in a microwave zone in the presence of air directly from the extruder, then passed through a longer heated air tunnel to complete the cure of the elastomeric profile.
- the method for manufacturing the article may be performed in a hot air tunnel, or any other apparatus.
- test method ASTM D5289 -12 "Standard Test Method for Rubber Property- Vulcanization Using Rotorless Cure Meters" was used.
- Test method ASTM D6204 was used with either a 0.5 degree or 1.0 degree arc and 100 cpm frequency of oscillation at cure temperatures appropriate for the curative system, e.g., 185 ° C for the examples below.
- MgO Magnesium Oxide Naugard ® 445 is 4,4'-bis(a,-dimethylbenzyl)diphenylamine, an antioxidant from Chemtura phr means parts of ingredient added for every 100 parts of pure rubber in the formulation.
- Vamac ® DP is a peroxide curable poly(ethylene acrylic) elastomer from Chemours
Abstract
Description
Claims
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US15/531,755 US10563039B2 (en) | 2014-12-09 | 2015-12-03 | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
CN201580066459.4A CN107001685B (en) | 2014-12-09 | 2015-12-03 | The composition and method of cross-linked polymer in the presence of aerial oxygen |
JP2017530730A JP6707541B2 (en) | 2014-12-09 | 2015-12-03 | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
BR112017012184-0A BR112017012184B1 (en) | 2014-12-09 | 2015-12-03 | COMPOSITIONS AND METHODS FOR RETICULATING POLYMERS IN THE PRESENCE OF ATMOSPHERIC OXYGEN |
EP15866456.5A EP3230356B1 (en) | 2014-12-09 | 2015-12-03 | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
ES15866456T ES2886573T3 (en) | 2014-12-09 | 2015-12-03 | Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen |
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WO2019190620A1 (en) * | 2018-03-26 | 2019-10-03 | Fina Technology, Inc. | Curable low sulfur liquid rubber compositions and methods of manufacturing the same |
WO2019202405A1 (en) | 2018-04-16 | 2019-10-24 | Braskem, S.A. | Bio-based eva compositions and articles and methods thereof |
WO2019202406A1 (en) | 2018-04-16 | 2019-10-24 | Braskem S.A. | Bio-based elastomeric eva compositions and articles and methods thereof |
CN111886297A (en) * | 2018-03-13 | 2020-11-03 | 诺力昂化学品国际有限公司 | Solutions containing dyes |
WO2021048634A1 (en) | 2019-09-11 | 2021-03-18 | Braskem S.A. | Very soft eva foam and methods thereof |
US11078349B2 (en) | 2019-04-24 | 2021-08-03 | Fina Technology, Inc. | Curable low sulfur liquid rubber compositions |
WO2022069949A1 (en) | 2020-10-02 | 2022-04-07 | Braskem S.A. | Ultrasoft eva foam formulation and methods thereof |
WO2022130027A1 (en) | 2020-12-18 | 2022-06-23 | Braskem S.A. | Polyethylene copolymers and terpolymers for shoes and methods thereof |
FR3132103A1 (en) * | 2022-01-25 | 2023-07-28 | Arkema France | Peroxide formulations with anti-scorch properties |
US11746197B2 (en) | 2019-10-15 | 2023-09-05 | Braskem S.A. | Bio-based EVA compositions and articles and methods thereof |
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US11325009B2 (en) | 2019-12-11 | 2022-05-10 | Acushnet Company | Golf ball and method of making same |
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Cited By (16)
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EP3230356B1 (en) | 2021-06-30 |
EP3230356A4 (en) | 2018-07-25 |
US10563039B2 (en) | 2020-02-18 |
US20170267832A1 (en) | 2017-09-21 |
EP3230356A1 (en) | 2017-10-18 |
CN107001685B (en) | 2019-09-27 |
ES2886573T3 (en) | 2021-12-20 |
JP6707541B2 (en) | 2020-06-10 |
BR112017012184A2 (en) | 2018-01-16 |
CN107001685A (en) | 2017-08-01 |
TWI756166B (en) | 2022-03-01 |
JP2017537202A (en) | 2017-12-14 |
TW201620996A (en) | 2016-06-16 |
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